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Technology offers several potential benefits for learning, including improved learning outcomes, enhanced teaching strategies, and the development of 21st-century skills for both students and educators. However, once the novelty of the device fades, the distractions of the classroom become too difficult to resist, and the teachers’ knowledge of relevant technological resources becomes antiquated, will students still engage and feel motivated to participate in their learning? The purpose of the current study is to investigate the following research questions: “To what extent is the frequency of one-to-one Chromebook use in a teacher’s classroom associated with teacher perspectives of academic self-motivation and perseverance?” and “To what extent are teacher and school characteristics associated with teacher perspectives of academic self-motivation and perseverance?” This research provides insight into and implications of how technology integration influences student motivation and the broader educational environment.